House holiday rentals in Chesterfield

A spacious outdoor area features a hot tub alongside a wooden pod structure. Stone tiles lead to steps that access the hot tub, while a small table can be seen nearby. Natural greenery borders the patio, providing a serene backdrop.

4.96 out of 5 average rating, 160 reviews

Spa Home with Hottub, Sauna Pool Table

Spa home with sauna, hottub, all modern amenities, on the edge of the Peak District and just 5 minutes walk from Chesterfield train station. 1pm check-in. Perfect for all experiences, extra large bedrooms. There is full-sized pool table, BBQ area, Sonos music, log-burner, open-plan kitchen and living areas. Ideal for several families or large group getaways. Prime location allows you to enjoy the Derbyshire countryside whilst being within walking distance of a multitude of cafes, shops and bars.

4.93 out of 5 average rating, 562 reviews

A bright upstairs bedroom features a super-king size bed with a patterned duvet and cotton bedding. A large window offers views of greenery. A cozy window seat is complemented by nearby built-in storage filled with books, enhancing the spacious feel of the room.

Home in Nether Edge

The Old Coach House. 5-star. Parking. EV charger.

“Loved staying here”. Off street parking. Ultra fast WiFi. Perfectly located in leafy Nether Edge village, 10 minutes from city centre and Peak District. Near to local shops, pubs, cafés and restaurants. Everything you need for the perfect stay: Private off-street parking: Yes. Big comfortable beds: Yes. Powerful shower: Yes. Washing machine: Yes. New kitchen: Yes. Spotlessly clean: Yes. Ultra-fast 1GB fibre optic broadband/Wi-Fi: Yes. Ev charger: Yes. Charm, character, history? Yes. Yes. Yes!

4.87 out of 5 average rating, 320 reviews

A spacious garden area is visible, featuring a variety of colorful flowers in pots, including bright yellow and pink blooms. A well-maintained lawn extends into the distance, accompanied by tree line and greenery. A soft play structure and garden shed are also included in the scene.

Home in Wingerworth

Oakdale - Our Quest retreat

Idyllically situated at the entrance to Hardwick Wood, Wingerworth, 2 miles from Chesterfield and all amenities, yet totally secluded. Close to Chatsworth & Peak District. Fully fitted kitchen all appliances including tumble drier & dishwasher. Underfloor zoned central heating. Log burner. Fully fitted bathroom with bath and shower. Separate shower/wc. Fully fitted bedrooms with ample wardrobes and drawers ideally suited to a family of 4. Sleeps 4 in one double and 1 set of bunks, cot available

4.98 out of 5 average rating, 128 reviews

A spacious living area features two black leather sofas facing a central coffee table. A large smart TV is mounted on the wall, displaying a colorful landscape, while soft lighting highlights the textured wall panels. Two light-colored armchairs complement the seating arrangement.

Home in Catcliffe

Sheffield Charming Detached 4bd Home

Welcome to our modern, spacious home, designed to provide a comfortable and memorable stay. Whether traveling with family, friends, or for work, you'll find everything you need for a relaxing visit. Amenities You'll Love: - Effortless self check-in with a secure digital lock - Fiber-optic WiFi – ideal for work or streaming shows. - Fully stocked essentials – tea, coffee, shampoo, body wash, conditioner, towels. - Equipped kitchen including– cookware, utensils, a 5-hob cooker, and dishwasher

Home in Ashford in the Water

The exterior of The Old Chapel is showcased, with its distinctive stone façade and original Gothic-style windows. Lush purple flowers border the pathway, while iron railings enhance the charming entrance. Sunlight filters softly, highlighting the architectural details and creating a serene ambiance.

4.99 out of 5 average rating, 158 reviews

The Old Chapel Luxury Retreat

Introducing The Old Chapel: Following the success and glowing reviews of the Old Bank Bakewell, we embarked on a quest for another unique stay. Enter The Old Chapel, a labor of love renovation resulting in a charming three-bedroom, all-ensuite stay unlike any other. Perfect for short getaways or week-long stays. Enjoy peaceful nights in king-sized beds fitted with luxurious 500-thread-count sheets. Each en-suite features spacious dual showers, fluffy robes, and slippers for ultimate relaxation.

The exterior of the stone cottage is featured, showcasing its classic design with multiple windows and a welcoming entrance. Hanging flower baskets add a touch of greenery, while the surrounding landscape displays lush grassland and rolling hills in the distance.

4.85 out of 5 average rating, 415 reviews

Runner Duck Cottage

A bright and airy cottage, comprising of two open plan rooms, a separate shower/WC. The kitchen area is equipped with hob, oven, fridge & microwave. In the downstairs lounge area there is a double pull out sofa bed, TV /DVD. Upstairs there is a king size bed & adjoining shower room/WC. Gas central heating. All bed linen, towels, and a welcome pack are provided. A charming little cottage for up to 4 people. Well behaved dogs are welcome. Immediate access to miles of footpaths & stunning views.

5.0 out of 5 average rating, 248 reviews

A spacious detached house is surrounded by lush greenery and landscaped grounds. The exterior features a stone facade, slate roof, and charming gardens with flowering plants. Free-roaming chickens are visible, adding a rural charm to the serene setting under a clear blue sky.

Home in Youlgreave

The Stables House, Lomberdale Hall. 4 to 7 guests

Spacious detached private house, 3,000 sq ft/ 275 sq m. Own drive. 3 acres of grounds. Log burner (fuel provided) Front, back and garden doors; Entrance hall, sweeping staircase, beautiful sitting room, library stuffed with books, 3 large bedrooms (Vispring beds) plus 3 fab bathrooms with baths & separate showers - plus a single bed downstairs. Warm kitchen, utility room & larder. Antique furniture, lovely curtains. Perfect for families, couples, groups. Walking galore! 3 Pubs in the village.

A charming stone barn exterior is framed by lush greenery. The building features several windows and is adorned with climbing vines and red leaves, creating a natural connection with its surroundings. A stone pathway leads to the entrance, enhancing the inviting appearance.

4.92 out of 5 average rating, 152 reviews

Hugo’s Luxury Barn

Welcome to Hugo’s Barn at Knabb Farm, a luxurious and tranquil countryside retreat in the heart of the Peak District. Perfect for couples, families and dog lovers looking to escape, relax and enjoy the beautiful surrounding countryside. Located just a short drive from Bakewell, Chatsworth, Matlock and Matlock Bath, Hugo’s Barn offers the perfect combination of peaceful surroundings while still being within easy reach of some of the Peak District’s most popular attractions, walks and villages.

An inviting living space is featured, showcasing a modern dining table and chairs alongside a vibrant red sideboard. A cozy armchair and a striped lounge chair add comfort, while softly illuminated pendant lights enhance the room's ambiance. Natural light filters through a window adorned with gray curtains.

4.91 out of 5 average rating, 114 reviews

Bright - 2 Bedroomed House in Derbyshire

Your family will be close to everything when you stay at this centrally located town house within walking distance from Chesterfield's iconic market town. This 2 bedroomed modern home has everything you need and is the perfect base for visiting all the local attractions Derbyshire has to offer. Right on the edge of the Peak District it boasts a 20 minute drive to Chatsworth House and many more. Along with all the wonderful bars, restaurants, gift & coffee shops all within walking distance.

A comfortable living area is furnished with a gray sectional sofa and two leather armchairs. A glass coffee table is positioned centrally, and a wooden cabinet stands against the wall, adding storage space. Double doors lead to the outside, allowing natural light to enter.

4.96 out of 5 average rating, 352 reviews

The Long Hall 2 bed ground floor annexed apartment

Long Hall has been lovingly converted into a 6-person, ground floor, annexed apartment, within a quiet housing estate, a short distance from the Peak District. Two large double bedrooms, with rainfall shower en-suites, and a large open-plan living area dining and kitchen area and a large, shared enclosed patio and garden area Long Hall suits leisure and tourist staycations, as well as trade or professional workers, who wish for a home from home. SKY Sports and Movies included

4.89 out of 5 average rating, 297 reviews

A view from a bridge showcases a serene countryside scene with a stone cottage nestled among lush greenery. The vibrant leaves of trees frame the picturesque surroundings, while the calm waters of the river reflect the natural beauty. The distant hills provide a backdrop.

Home in Grindleford

Bridgefoot Cottage - Wild Swimming & Hot Tub

Bridgefoot is a beautiful 17th century cottage situated in the Peak District. Guests have full use of the property including a modern, fully equipped kitchen, perfect for entertaining. There is also an exceptionally comfy and cosy sitting room, equipped with 2 sofas (one of which is a double sofa bed) a log burner and a Smart TV. The master bedroom boasts a luxurious four poster bed and an ensuite bathroom. Next door is a spacious second bedroom with two comfortable single beds.

4.96 out of 5 average rating, 169 reviews

Home in South Yorkshire

The Little Lodge

Kick back and relax in this calm, stylish space. The Little Lodge is a brand new renovated annex attached to a charming Victorian Lodge from the 1800s. Situated in a picturesque and peaceful conservation area on a private road in the leafy suburb of Ranmoor Sheffield. The Little Lodge is only 15minutes away from Sheffield's main train station and sits of the foothills of South Yorkshire's famous Peak District. Ideal for a city break or a Rambler's retreat.

Popular amenities for Chesterfield house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.84 out of 5 average rating, 289 reviews

An indoor heated swimming pool is framed by large wall-length windows, offering ample natural light. The pool features a curved shape with metal steps leading into the water. Lounge chairs are positioned nearby, inviting relaxation beside the serene water.

Home in Rowsley

The Round House - family house with indoor pool

4.93 out of 5 average rating, 57 reviews

A spacious dining area features a long wooden table with comfortable upholstered chairs, accommodating multiple guests. A large vase filled with flowers serves as a focal point. The open kitchen can be seen in the background, showcasing modern appliances and a warm aesthetic.

Home in Brassington

Spacious Dog Friendly Cottage by Carsington Water

4.9 out of 5 average rating, 80 reviews

Home in Winster

Charming 6-Bedroom Winster Village, Peak District

The exterior of Haddon Grove Farmhouse is showcased, featuring stone walls and a lush green lawn. A pathway leads to the entrance, flanked by colorful flowers. Plantings and trees provide a natural backdrop, with comfortable outdoor seating visible for relaxation.

Home in Bakewell

4.82 out of 5 average rating, 17 reviews

Haddon F'house - shared heated pool & games room

A sitting room is presented with cozy seating arrangements on either side. A glass coffee table is centered on an ornate area rug, while a woodburning stove is positioned against a warm-toned wall. A television is mounted nearby, enhancing the room’s inviting atmosphere.

4.8 out of 5 average rating, 5 reviews

Pippinwell

Home in Finningley

New place to stay

Luxury apartment with private pool and garden.

Home in Hopton

Butler's Quarters

Home in Hopton

The Granary

Weekly house rentals

4.98 out of 5 average rating, 313 reviews

Home in Rowsley

Panoramic views, calf feeding, Bakewell Chatsworth

5.0 out of 5 average rating, 169 reviews

A charming stone exterior of the Coach House is highlighted, featuring a large arched entrance and a row of windows. The surrounding trees and blue sky create a serene environment, while the pathway leading to the entrance is flanked by stone walls and greenery.

Home in Bakewell

The Entire Coach House at Middleton Hall

4.99 out of 5 average rating, 143 reviews

A large country house is set against a serene landscape, with well-maintained lawns and pathways leading to its entrance. Surrounding greenery complements the stone façade, while benches are positioned along the garden for relaxation. The peaceful setting invites quiet moments outdoors.

Home in Woolley Moor

Oldfield House Woolley Moor, Ashover, Derbyshire

4.91 out of 5 average rating, 122 reviews

A warm living area is adorned with an orange sofa, layered with decorative pillows. A low table rests atop a patterned rug, while a guitar leans against a natural wood shelf featuring books and plants. Two windows invite natural light into the space.

Home in Grindleford

Peak District Home from Home!

4.91 out of 5 average rating, 268 reviews

A living room area features a dark gray sofa with plaid cushions, positioned beside a small white coffee table. A flat-screen TV is mounted on a wall unit, while light streams through a window with white shutters, creating a bright and welcoming space.

Home in Totley

Charming fully equipped home 5min to Peak District

4.84 out of 5 average rating, 364 reviews

The entrance to the cottage features a classic stone facade, complemented by a wall-mounted trellis and a decorative lantern. A wooden bench sits nearby, offering a place to relax. On the right, a wooden gate leads to a scenic view of the surrounding countryside.

Home in Rowsley

Beautiful 19th-Century Terraced Cottage

4.99 out of 5 average rating, 134 reviews

A charming stone cottage is visible, framed by lush greenery and flowering plants. The two-story structure features a sloped roof and a chimney, with a pathway leading to the entrance. Rolling hills are seen in the background, under a partly cloudy sky.

Home in Ashover

Country Cottage with great outside space & views

4.98 out of 5 average rating, 333 reviews

The charming stone cottage features a symmetrical facade with large windows, allowing natural light to fill the interior. A spacious patio area is visible in front, providing ample outdoor space. The roof is covered in slate, complementing the warm stone exterior.

Home in Great Longstone

Chert Cottage, Great Longstone, Bakewell Peak Dist

Private house rentals

4.99 out of 5 average rating, 201 reviews

A vibrant green snooker table is positioned in the center of the games room. A triangle of red balls rests at one end, with a single black ball placed nearby. A large television and seating area are visible in the background.

Home in Ecclesfield

Exclusive Detached Retreat+Games Room M1J35 1.5m

A rustic stone cottage is set against a backdrop of rolling hills. A spacious wooden deck extends from the cottage, surrounded by lush green grass and trees. Soft sunlight filters through the foliage, creating a serene outdoor environment.

4.83 out of 5 average rating, 498 reviews

Cosy cottage, stunning views near Chatsworth

4.91 out of 5 average rating, 127 reviews

The spacious bedroom features a comfortable bed with plush bedding and a tufted headboard. Natural light filters through adjoining windows, illuminating the neutral decor. A decorative mirror and vintage-style vanity table enhance the ambiance, while exposed beams add character to the high ceiling.

Home in Bolsover

The Cottage - Derbyshire

A cozy living area is presented with a brown sofa adorned with decorative cushions. A wooden coffee table sits in front, complemented by a patterned area rug. A wall-mounted television and a decorative shelf enhance the space, which is warmed by a stove and illuminated by natural light.

4.89 out of 5 average rating, 92 reviews

The Beehive

4.95 out of 5 average rating, 42 reviews

Charming 18th century stone cottage

4.86 out of 5 average rating, 42 reviews

A light-filled living area features a comfortable sectional sofa in soft gray, complemented by decorative pillows. A dark coffee table occupies the center space, while large glass doors open to a private outdoor seating area, enhancing the connection to nature.

Home in Brimington

Blissful Barry’s

The exterior of the brick house is showcased, featuring a charming door with a small balcony above. Large windows allow natural light in, while the well-maintained driveway provides ample space for parking. A clear blue sky enhances the welcoming appearance of the property.

4.97 out of 5 average rating, 64 reviews

Home in Chesterfield

A warm living space is depicted, featuring a beige sofa and a brown recliner chair. A cozy fireplace is visible, with a small dining table in the foreground. Wall decorations include heart-shaped ornaments, and a staircase leads to the upper level.